10. Joe Cronin
Former Portland Trail Blazers guard Damian Lillard had publicly announced his desire to be traded and join the Miami Heat at the beginning of July, from the team where he had played for 11 seasons. He believed that the Blazers were not constructing a winning team around him. However, negotiations throughout the summer did not yield any fruitful results.
On September 5th, Lillard and Trail Blazers General Manager Joe Cronin had a private meeting at Lillard's home to discuss and clarify their respective positions. During the meeting, Cronin emphasized that any potential deal with Miami would require significant assets from the Florida team. Lillard expressed his preference to rescind his trade request and return to the Trail Blazers if a deal couldn't be reached with the Heat, but Cronin firmly stated that there was no possibility of him coming back.
This news came as a shock to Dame, who found it disheartening to hear that he couldn't return. Despite this setback, he didn't want to be in a place where he wasn't wanted, so he decided to end the meeting. Cronin admitted feeling surprised by Lillard's trade request and specifying Miami as the desired destination complicated the process of securing the best possible return.
After the trade, Lillard shared a lengthy farewell message on social media, which did not mention Cronin. In July, Dame had expressed his desire to play for the Miami Heat, but after waiting for nearly three months, he ended up being traded elsewhere.
The outcome was undoubtedly disappointing for Lillard, but it was even more surprising for the Heat, who had openly expressed their interest in adding the All-Star player to a team led by Jimmy Butler and Bam Adebayo. The fact that Lillard ended up with another Eastern Conference contender, the Milwaukee Bucks, alongside Giannis Antetokounmpo, and the subsequent effect of Jrue Holiday joining the Boston Celtics further hindered Miami's fortunes.
Throughout the discussions regarding a potential Lillard trade, the Heat and Trail Blazers never seemed to be on the same page, and there were reportedly some contentious exchanges originating from Portland.
The Phoenix Suns, in a three-team trade, facilitated the acquisition of Holiday, Deandre Ayton, Toumani Camara, a 2029 first-round draft pick, and future swap rights for the Trail Blazers. Subsequently, the Trail Blazers traded Holiday to the Celtics in exchange for Malcolm Brogdon, Robert Williams III, and two additional first-round picks.
Although Lillard remained hopeful about a potential deal with the Heat, he had to face the reality that it might not materialize. Cronin, on the other hand, opted for the Milwaukee package in a three-team blockbuster trade, which turned out to be the biggest transaction during his tenure as general manager. In the end, everything seemed to work out, and Dame now has the opportunity he has always desired - the chance to compete for a championship.